Issue 30, 2012
From the journal:

Organic & Biomolecular Chemistry

Synthesis of 1,2,4-triazines and the triazinoisoquinolinedione DEF ring system of noelaquinone†‡§

Liming Cao,a   John P. Maciejewski,a   Stephan Elzner,a   David Amantinia  and  Peter Wipf*a  

* Corresponding authors

a Department of Chemistry and Center for Chemical Methodologies and Library Development, 219 Parkman Avenue, 15260 Pittsburgh, PA, USA
E-mail: pwipf@pitt.edu
Fax: +1 412 624 0787
Tel: +1 412 624 8606

Abstract

The intramolecular Staudinger-aza-Wittig reaction is used for a general synthesis of 1,2,5,6-tetrahydro-1,2,4-triazines, a structural motif reported for the natural product noelaquinone. The DEF moiety of noelaquinone was obtained in 13 steps and 2% overall yield, and the structure of the synthetic product was confirmed by X-ray analysis.

Graphical abstract: Synthesis of 1,2,4-triazines and the triazinoisoquinolinedione DEF ring system of noelaquinone

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Article information

DOI
https://doi.org/10.1039/C2OB25353D
Article type
Communication
Submitted
20 Feb 2012
Accepted
19 Mar 2012
First published
20 Mar 2012

Org. Biomol. Chem., 2012,10, 5811-5814

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Synthesis of 1,2,4-triazines and the triazinoisoquinolinedione DEF ring system of noelaquinone

L. Cao, J. P. Maciejewski, S. Elzner, D. Amantini and P. Wipf, Org. Biomol. Chem., 2012, 10, 5811 DOI: 10.1039/C2OB25353D

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